Holiday houses in Wicker Park, Chicago

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Wicker Park, Chicago

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Lincoln Park

5 out of 5 average rating, 13 reviews

Top Floor in Historic Old Town!

KristenRating, 5 stars1 day ago

Heather’s place was perfect. It was very quiet which is an absolute for us when we travel. The location was also great for visiting my family in Lincoln Park. Easy walking to armitage shops, restaurants etc. I appreciated that Heather provided parking stickers and street parking was very easy. I will definitely book again.

Top Guest favourite

Home in Avondale

5 out of 5 average rating, 12 reviews

Alluring Avondale Abode

MichaelRating, 5 stars3 weeks ago

Beth’s home was perfect for our group trip, which centered around cooking together for a Passover Seder! The kitchen had great appliances and equipment, with the space for many of us to cook at once. The house had everything we needed and we were all comfortable.

Superhost

Home in Austin

4.85 out of 5 average rating, 68 reviews

A Comfortable Stay While You are Away in Oak Park

KarenRating, 5 stars3 weeks ago

The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

Guest favourite

Guesthouse in Evanston

4.85 out of 5 average rating, 34 reviews

Tiny house in West Village Arts District

JoelRating, 5 stars4 months ago

Lisa was a great host and this is a great place. It's a small house, but worked great for what we needed it for and was close to our family that live in Evanston. It was also a great price. Additionally, there were games which was nice because we had our child with us. I would definitely recommend this place and I will be staying here again when we're in Evanston, hopefully Lisa's schedule will be open!

Superhost

Apartment in Lake View

4.88 out of 5 average rating, 75 reviews

Spacious 2 Bed Apartment, Perfect Location

BobRating, 5 stars1 month ago

This is a quirky, comfortable place. It’s full of great books, interesting decor and Chicago charm. The apartment is quite large, it’s on the ground floor and there is back door access to the alley from the kitchen. The kitchen was full of cookware and there was a gas stove. I appreciated the coffee pot and large tin of Costco coffee. There was also a great selection of teas as well as many interesting mugs to choose from.

Guest favourite

Guesthouse in Oak Park

4.95 out of 5 average rating, 104 reviews

O'Malley Oasis!

AndreaRating, 5 stars4 months ago

Clean, beautiful space. Has everything needed and the most comfortable seating space to relax. Clear instructions, easy parking. Be aware that there are several stairs to enter as seen in the pictures. They are well maintained with a handrail. This was not an issue at all for us but could be for someone with mobility limitations. Otherwise one of the best places I have stayed in Oak Park. Hope it is available when I come back.

Top Guest favourite

Apartment in Irving Park

4.96 out of 5 average rating, 281 reviews

Spacious 1BR apartment in a central location

GilRating, 5 stars1 month ago

I have stayed in a number of AirBnB‘s throughout the years, this may have been my favorite stay. There is absolutely everything you would need for a comfortable stay. Everything is clean. Alex is a five-star communicator. It is a busy little neighborhood, but the bedroom is toward the back of the apartment. I heard nothing but dead silence at night.

Holiday rentals for every style

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Popular amenities for Wicker Park, Chicago holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Wicker Park, Chicago's top sights

Big Star31 locals recommend

Mariano's12 locals recommend

Revolution Brewing - Brewpub18 locals recommend

Parson's Chicken & Fish22 locals recommend

Pequod's Pizza65 locals recommend

Piece Brewery19 locals recommend

Other great holiday rentals in Wicker Park, Chicago

Superhost

Home in West Lawn

4.93 out of 5 average rating, 40 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars3 weeks ago

Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗

Guest favourite

Home in Elmhurst

4.87 out of 5 average rating, 23 reviews

Enamored in Elmhurst

EmilyRating, 5 stars1 week ago

We had a great stay. The house was perfect for our group - 4 adults and 1 baby. Very clean, with great facilities. The wireless chargers were so helpful as we were international visitors. Also, the provision of tooth brushes, mouthwash and razors in the bathroom was a great bonus. Plenty of towels, comfortable beds and lovely location near the Prairie path made it a wonderful stay.

Guest favourite

Apartment in West Town

4.85 out of 5 average rating, 131 reviews

Condo with private terrace, free WIFI and parking

MatthewRating, 5 stars2 weeks ago

Mark's place was a real find: The location was terrific, and the home itself was quirky, quiet, and comfortable. We found a great bar and a very good lunch spot within literally a block of the place, and there were dozens more we didn't get to explore. The roof deck is a pure delight: The weather wasn't great during our visit, but whenever it was halfway decent we made ourselves comfortable up there. Having two full bathrooms was a boon for a party of four. The neighbor who takes care of the place was incredibly friendly and helpful, too. I was honestly sad to leave. Highly recommend it!

Guest favourite

Apartment in Albany Park

4.86 out of 5 average rating, 42 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

Superhost

Apartment in Jefferson Park

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago

Peaceful, felt like home, very spacious and comfortable

Superhost

Home in Logan Square

4.84 out of 5 average rating, 100 reviews

California Cottage/4br prime location Logan Square

JeniRating, 5 stars3 weeks ago

Daniel’s house was perfect for what we needed. Seven adult women were comfortable and enjoyed the open table space. Bathrooms in basement and main level were clean, and plenty of linens and towels were supplied for the three nights we were there. Nice location for easy pickups and stores with delivery nearby for quick groceries. Also check out Diversey House nearby - great food and drinks! Thanks for a great weekend getaway!

Superhost

Condo in East Rogers Park

4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars4 months ago

This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.

Superhost